2-pyridyinitrene from tetrazolo[1,5-a]pyridine and Pyrido[2,3-a][1,2,4]oxadiazol-2-one

被引:17
作者
McCluskey, Adam [1 ]
Wentrup, Curt [1 ]
机构
[1] Univ Queensland, Sch Mol & Microbial Sci, Brisbane, Qld 4072, Australia
关键词
D O I
10.1021/jo800899t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Flash vacuum thermolyses of tetrazolo[1,5-a]pyridine and pyrido[2,3-a][1,2,4]oxadiazol-2-one generate 2-pyridylnitrene, which was detected by Ar matrix ESR spectroscopy. The thermolysis products are 2-aminopyridine, Z- and E-glutacononitriles, and 2- and 3-cyanopyrroles. The products are formed in the same ratios from the two precursors.
引用
收藏
页码:6265 / 6267
页数:3
相关论文
共 16 条
[1]   2-quinolyl- and 1-isoquinolylnitrenes: Ring expansion and ring opening in heteroarylnitrenes [J].
Addicott, C ;
Reisinger, A ;
Wentrup, C .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1470-1474
[2]   2-pyrazinylnitrene and 4-pyrimidylnitrene. Ring expansion to 1,3,5-triazacyclohepta-1,2,4,6-tetraene and ring opening to (2-isocyanovinyl)carbodiimide [J].
Addicott, C ;
Wong, MW ;
Wentrup, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8538-8546
[3]   PYRROLE CHEMISTRY .2. 2-PYRROLECARBONITRILE, 1-METHYL-2-PYRROLECARBONITRILE, AND THEIR NITRATION PRODUCTS [J].
ANDERSON, HJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1959, 37 (12) :2053-2058
[4]   3-pyridylcarbene and 3-pyridylnitrene: Ring opening to nitrile ylides [J].
Bednarek, P ;
Wentrup, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9083-9089
[5]   A C-13 AND H-1-NMR STUDY OF THE GEOMETRIES OF THE 1,3-DICYANOALLYL ANION - THERMAL AND PHOTOCHEMICAL INTERCONVERSION [J].
BOATE, DR ;
HUNTER, DH .
ORGANIC MAGNETIC RESONANCE, 1984, 22 (03) :167-170
[6]   REARRANGEMENT OF HETEROARYL NITRENES FORMED BY PYROLYSIS OF FUSED OXADIAZOLONES AT 600 DEGREES C [J].
BROWN, RFC ;
SMITH, RJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (03) :607-&
[7]   NITROGEN SCRAMBLING IN 2-PYRIDYLNITRENE [J].
CROW, WD ;
WENTRUP, C .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (23) :1387-&
[8]  
DENHERTOG HJ, 1966, TETRAHEDRON LETT, P4325
[9]   HETARYLNITRENES .6. PYRIDYLNITRENES - MECHANISM OF RING CONTRACTION TO CYANOPYRROLES [J].
HARDER, R ;
WENTRUP, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (05) :1259-1260
[10]   ELECTRON-SPIN-RESONANCE OBSERVATION OF THERMALLY PRODUCED TRIPLET NITRENES AND PHOTOCHEMICALLY PRODUCED TRIPLET CYCLOHEPTATRIENYLIDENES [J].
KUZAJ, M ;
LUERSSEN, H ;
WENTRUP, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (05) :480-482